title: Preparation of D-galactofuranosyl nitromethanes: a revision and a new approach.
abstract: Sodium methoxide-promoted methanolysis of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol peracetate rapidly and nearly quantitatively accumulates 7-deoxy-6-O-methyl-7-nitro-L-glycero-L-galacto-heptitol. The prolonged treatment then provides 76% of D-galactofuranosyl nitromethanes and finally results in the equilibrium of 77% of β-D-galactopyranosyl nitromethane and 7-9% of three other tautomeric D-galactosyl nitromethanes. Thermal treatment of 7-deoxy-7-nitro-L-glycero-L-galacto-heptitol in boiling water peaks at a 58% content of D-galactofuranosyl nitromethanes and ends in a similar equilibrium mixture of four D-galactosyl tautomers. The relevant kinetic parameters of the latter transformation are determined by a curve fitting using the nonlinear least-squares Marquardt-Levenberg algorithm.
authors.affiliation: Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia.
authors.forename: Michal
authors.initials: M
authors.lastname: Vojtech
authors.forename: Mária
authors.initials: M
authors.lastname: Petrušová
authors.forename: Ivan
authors.initials: I
authors.lastname: Valent
authors.forename: Božena
authors.initials: B
authors.lastname: Pribulová
authors.forename: Ladislav
authors.initials: L
authors.lastname: Petruš
mesh_terms: D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D006001:Glycoconjugates; D009595:Nitroparaffins; D008697:Methane; C008640:nitromethane; D000432:Methanol